Tyler stood on Catherine's rooftop terrace, his confession hanging in the night air between them like a challenge. "It's gotten loose," he said, his voice barely audible over the city sounds below. "After three months of regular wear, my cage doesn't fit the same way anymore."
Catherine set down her wine glass, her eyes immediately dropping to his crotch with predatory interest. "Show me."
Without hesitation, Tyler unbuckled his belt and pushed down his jeans. The familiar cage hung around his diminished length, clearly too large now for its intended purpose. Catherine circled him slowly, examining the gap between steel and flesh with clinical fascination.
"Chastity shrinkage," she murmured, running her finger along the loose metal. "Your cock has actually gotten smaller from being denied so much." Her touch sent electricity through him despite the barrier. "I love it."
Tyler's breathing quickened as she continued her inspection. "I found something online… accessory rings that work with this cage. Different sizes to make it tighter again."
"Clever boy." Catherine's hand cupped the loose device, making him gasp. "You want to keep using this particular cage?"
"Yes, Mistress. It's perfect, just needs…"
"Needs to grip your pathetic little dick properly again." She squeezed the cage firmly, watching him strain uselessly against the steel. "Order the smallest ring they make."
Her other hand found his nipple through his shirt, pinching hard enough to make him cry out. The combination of her touch and the loose cage created a maddening sensation… almost stimulation, but not quite enough.
"Please," Tyler whimpered as she worked both his nipples now, the cage shifting with each movement but providing no real friction.
"Please what?" Catherine's voice carried that dangerous edge he knew so well. "You want me to unlock you? Let you cum like a real man?"
"No, I… I want the new ring. Want to feel trapped again properly."
She laughed, the sound sharp in the night air. "Such a good little masochist. You're actually begging me to make your prison tighter." Her fingers found the padlock, rattling it against the loose metal. "Two-day shipping?"
Tyler nodded frantically as she continued tormenting his nipples, the oversized cage mocking his desperate attempts at arousal.
"Then you'll spend two more days like this… loose, unsatisfied, knowing that soon you'll be squeezed even tighter than before." She released him abruptly, leaving him aching and desperate. "Now put your pants back on. I want to watch you suffer through dinner knowing what's coming."